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Key west 5/1-5/3

Hello Guys,
The wife and I are headed down to key west for our anniversary sun through Wednesday morning and I was hoping someone could help me out. We spent our first ever vacation together down on Duvall for her 21st and had a blast and I have been back multiple times in the last 9 years. Normally we go to Islamorada for back country and offshore fishing and Key west is mainly a shopping and drinking trip. This time we are staying at Simonton court hotel and plan on relaxing, eating, drinking and we have decided to book a charter and fish this time. We both fish regularly here in Naples mostly back country ( snook, reds, trout, etc) and occasionally red grouper, snapper, etc off shore.
I would really like to either a) get her a tarpon on the flats ( we get them here off the beach and have done bridge fishing in the upper keys) or b) maybe a sailfish offshore.
I was just wondering if you guys could point me in the right direction.
Also we have been to all the usual spots down there but one night we want to do a good dinner. Last time I was there on business we ate at La trattoria and it was great.
Thanks,
Billy

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